“What Was Your Greatest Failure?” – Top 10 Interview Questions by Kary York, Insurance Resourcing

QUESTION #5: “What was your greatest failure?“ 

Ahh, the dreaded question. This one is even touchier than the weaknesses question because you have to admit a failure, not just a weakness. The trick with this question is to show how you learned from the failure and how you use the experience to help you make decisions today.


Tips to Answer this Interview Question:

Again, this requires you to prepare an example ahead of time. It should be work-related, but you can discuss a personal experience if it is closely related to a work-like event. For instance, if you didn’t graduate from college, perhaps you feel this is a failure or regret. If it’s unlikely that you’ll one day get a degree, then show how you keep yourself current with changes in the industry and new carrier products, how you have obtained insurance designations, etc.

If your failure example is work-related, make sure you set up the scenario so the employer understands the whole picture and doesn’t assume the worst. For example, suppose you had the idea to reorganize the work flow in your department. You need to show that you studied the problem, decided on a solution, implemented the solution, measured the results, found that it didn’t solve the problem, and decided to abandon the project in favor of a stronger option.

The key here is in the presentation. You do not want to come off as a victim. Do not blame others for the fact that something didn’t work. You must take ownership of the situation. Employers use this question to see how you react to and deal with adversity. Do you take responsibility for your decisions or blame the world for what went wrong? This is especially important since you most likely don’t know about the inner workings and politics of the firm at this point. Take the high road, even if your former company made decisions that derailed your project.
Most importantly, show how you made the decision to change course and quantify those results.  Then, show how you use the experience to guide your decision-making today.

Learn about the next interview question: “Why did you leave your previous position?”


About Kary York

Kary York is the President of Insurance Resourcing LLC. She graduated from Central Washington University with a bachelor’s degree in business and holds her Washington State Life and Disability license. She has over 18 years of successful insurance and sales recruiting experience and created the firm in response to the changing hiring and recruiting needs of the insurance industry.

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